MILLBURN, N.J. ( Stockpickr) -- When picking stocks, I will usually start by looking at one of more fundamental variables or by targeting a sector theme. While that may serve as my guide, another aspect to investment management is taking advantage of speculative opportunities. Sometimes it pays to take chances by allocating a small portion of your portfolio to high-risk, high-reward contrarian plays.For example, during the financial crisis, shares of Ford ( F) were being priced for bankruptcy, yet the company was not in the same sad state of affairs as General Motors ( GM) and Chrysler. Ford common and preferred stock was extremely cheap, and I bought some into the abyss. Later, I sold that stock for hefty profits. Casual dining chain Ruby Tuesday ( RT) was also in disarray. Investors were pricing in the demise of the company. What I saw at Ruby Tuesday was a new management team that was going to turn the company around. I was able to buy shares for $2 or less, and once that new management team did indeed turn the company around, I wound up selling those same shares at $10 and higher. >>5 Stocks Under $10 With Big Upside Potential Buying low-priced down-and-out stocks is like buying call options on a company's survival. I am now seeing similar opportunities in an entire country: Greece. The situation in Greece is akin to what happened in Latin America in the early 1990s, Russia in the late 1990s and even to the U.S. financial institutions a few years ago. Before I present my ideas, I want to put some parameters around this strategy. First, when adding these names to your portfolio, allocate an equal dollar amount for each stock. You cannot predict whether one or all of the stocks will pay off, so you want to spread our capital around so as not to miss or limit our opportunity for gains. Think of this money as lottery money. Allocate only a small portion of your total portfolio to these stocks because of the speculative nature of the strategy. Ideally, you'll get a hefty payout; should you lose, however, the damage to your portfolio will be small.